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Meet the 23-Year-Old Student Who Raised $25 Million in Democratic Losses

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Meet the 23-Year-Old Student Who Raised  Million in Democratic Losses

After the Democratic candidates in Florida’s special elections burned through millions and millions of dollars on the way to double-digit losses this week, some Democrats are asking where that money deluge came from — and where it all went.

The answer to both questions is, in part, a 23-year-old law student and dungeon master — in Dungeons & Dragons — with a lucrative side gig.

In between classes and fantasy play, Jackson McMillan is also the chief executive of Key Lime Strategies, a small fund-raising firm in Florida that scored big when it landed as clients the two Democratic nominees in the Florida congressional elections, Josh Weil and Gay Valimont. Mr. McMillan said they had combined to raise $25 million.

“We’ve built a juggernaut,” he said in an interview.

Along the way, Mr. McMillan has piled up critics far beyond his years. Much of the focus is on his unusual fee structure, which one top party official excoriated in a cease-and-desist letter as “exorbitant.” His firm received a 25 percent cut of “true profits” — the proceeds after fund-raising expenses — for both special elections.

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Mr. McMillan is unapologetic.

“A lot of the people who are critiquing me online are mad that it wasn’t them,” he said of raising so much money, which he said put a scare into Republicans and injected real money into long-neglected corners of a rightward-drifting state.

One secret ingredient to his firm’s success, Mr. McMillan explained, is Dungeons & Dragons.

“All the senior fund-raising strategists at my firm — myself, Ryan — we’re dungeon masters,” he said of his college friend and the firm’s chief operating officer, Ryan Eliason. “We run Dungeons & Dragons games. So we weave narratives and tales. It’s like our biggest hobby. We basically tell a really compelling story. And that’s what sets us apart from — that and a lot of technical analysis — is what sets us apart from some of our competitors.”

Others say the story his team spun up about Mr. Weil and Ms. Valimont made him a false-hope merchant who cashed in on the desperation of small Democratic donors wanting to fight the new Trump administration. These were lopsidedly Republican seats, which the G.O.P. won by more than 30 percentage points last fall and where Democrats faced near-impossible odds; the Republicans won by 14 percentage points on Tuesday.

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Stefan Smith, a digital strategist who is head of digital engagement at the American Civil Liberties Union, called the 25-percent-of-profits fee structure “absurd” and said the races had diverted donor money from more urgent priorities under false pretenses of competitiveness.

“Democrats are experiencing the largest trust gap we’ve experienced in a generation, and we are not going to win that back by letting predators roam freely across the digital ecosystem,” Mr. Smith said, speaking in his personal capacity. “It is on all of us to hunt them to extinction.”

There is no single standard for fund-raising contracts, but more typically, consultants earn a retainer and either a percentage of what is spent creating and placing ads, or a much smaller percentage of what is raised overall.

So just how much did Mr. McMillan’s firm clear?

“I don’t think I’m totally comfortable sharing that,” he said, waving off talk that it had amounted to a multimillion-dollar payout and saying that all of the bills had yet to be settled.

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“Don’t get me wrong,” he added. “My firm did well.”

Records show that by mid-March, the two campaigns had paid his firm $4.7 million, roughly 38 percent of their total spending.

Much of the money sent to Key Lime Strategies appears to have paid for fund-raising ads.

In the first 90 days of the year, Mr. Weil’s campaign was the single biggest political spender on Instagram and Facebook in the nation, spending $2.5 million. Ms. Valimont’s campaign was close behind, at $2.1 million.

Neither Mr. Weil nor Ms. Valimont returned calls for comment. Both sent written statements praising Mr. McMillan. Mr. Weil said the campaign’s payments to the company had covered polling and mailers, as well as email, text and social media messaging.

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“The work he did on this campaign should cement Jackson McMillan as the gold standard for Dem fund-raising and political coordination in the state of Florida for years to come,” he said. Ms. Valimont said the funds helped to boost “voter registration efforts that would never have garnered any investment under normal circumstances.”

It’s an adage of online political fund-raising that you have to spend money to make money. (And raising big money brings more media attention, which in turn can bring in more money.) The question is if quite that much needed to be spent. Records show the advertising blitz overwhelmingly went to raising more money rather than persuading Florida voters.

Both Mr. Weil and Ms. Valimont, for instance, spent far more on ads in California than in Florida, records show.

All told, the Weil campaign spent far less on local television ads, $1.5 million, than out-of-state online fund-raising.

At one point in the race, Representative Alexandria Ocasio-Cortez, Democrat of New York, said she was being featured in fund-raising appeals without her permission. And lawyers for David Hogg, a Democratic National Committee vice chair, wrote a cease-and-desist letter asking Mr. McMillan to pull ads featuring Mr. Hogg because he would not “lend his name to fund-raising efforts that divert substantial portions of the proceeds from a campaign to cover exorbitant fees for fund-raising consultants.”

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Mr. Hogg went even further in a post on X. “People like Jackson McMillan are the exact type of consultants who people say are the problem in our party,” he wrote.

In an interview, Mr. Hogg explained his decision to go after Mr. McMillan by name: “Nothing is going to change until we start calling these people out.”

Mr. McMillan said that the episode had been a “misunderstanding” and that the firm had pulled the ads and apologized. He noted that he and Mr. Hogg, 24, had risen in Florida politics at the same time and are of the same generation.

“We’re in the same space,” Mr. McMillan said. “And I would love to work together with Vice Chair Hogg more, and I think we have the same motives and goals, which is why I was very, very surprised to see his onslaught of attacks.”

Mr. McMillan is also the treasurer of the Florida Future Leaders PAC, a youth-organizing group formed last year. State records show the PAC paid Key Lime Strategies more than $534,000, roughly 65 percent of the group’s total expenses.

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Mr. McMillan defended his firm’s pay structure, which is listed on its website, as cheaper and “more ethical” than some rivals, who sometimes take a smaller cut of the total raised, regardless of what the campaign is netting.

Mr. McMillan said he had actually stumbled into the digital fund-raising business.

He was once an aspiring paleontologist at the University of Florida, where he said he had enrolled early as a 15-year-old after skipping some grades. But a trip to Wyoming for a dinosaur-bone dig was interrupted by a car accident, and he recalled rethinking his career choice as he removed glass shards from his arm.

He met his business partner and current roommate, Mr. Eliason, in college. They formed the Magic the Gatoring club, where students gathered to play the fantasy card game Magic the Gathering, and a quick bond followed.

Mr. McMillan filed the paperwork for Key Lime Strategies in June 2022 and began doing political field programs for local races, including some for the Tampa City Council. “It was a lot of work for not a lot of payoff,” Mr. McMillan recalled of early fund-raising efforts.

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But then came Ms. Valimont’s first long-shot bid for Congress, in 2024 against Matt Gaetz — a high-profile villain for many Democrats. Mr. McMillan, by then a full-time student, said it had been the “perfect contest” to experiment in.

Ms. Valimont raised $1.58 million. More than half — $812,824.15 — went to Key Lime Strategies.

She lost by 32 percentage points.

Then she ran in the special election, rehired Key Lime Strategies, raised millions more and lost again.

If fund-raising doesn’t work out, Mr. McMillian is already testing another business that he filed the paperwork for in January: using artificial intelligence to spot consumer complaints for potential lawsuits against “corporate bad actors.” “That is the kind of law that I am most familiar with,” he said, citing some courses and an internship last summer.

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Either way, he is betting on himself — and his Gen Z colleagues.

“I will put money on a 20-something in politics every day over someone who’s been doing this for 40 years,” Mr. McMillan said. “Give them an energy drink, and they will outwork you 10 to one.”

Kitty Bennett contributed research.

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Three more people charged with damaging Reflecting Pool after Trump’s multimillion-dollar restoration | CNN Politics

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Three more people charged with damaging Reflecting Pool after Trump’s multimillion-dollar restoration | CNN Politics

Three more people have been criminally charged with destruction of property at the Lincoln Memorial Reflecting Pool.

Officers say they detained Cameron Thiers, Sophie Dennison-Gibby and Justin Carreno one Saturday afternoon in June and described in court documents witnessing them peeling and removing pieces of blue paint from the Reflecting Pool.

One officer “witnessed Carreno reach down into the reflecting pool and pull up a piece of the blue paint,” according to the court documents.

The officer who detained Dennison-Gibby “found 1 additional piece of the reflecting pool liner” in her purse, the documents said.

All three incidents were recorded on the officers’ body worn cameras, they said in the court documents.

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Several “partnering law enforcement agencies assigned to the Reflecting Pool” working with US Park Police were involved in detaining the two men and one woman — including officers from Texas, Oklahoma, Montana and California.

One of the officers said in court documents that Thiers “admitted to removing a piece of blue sealant from the Reflecting Pool and still had it in his hand when I made contact with him.”

The three defendants were arraigned in court Wednesday and pleaded not guilty to the misdemeanor charges of destruction of property with a value less than $1,000. The judge ordered them to stay away from the Reflecting Pool.

Lawyers for Thiers and Dennison-Gibby declined to comment. CNN has reached out to Carreno’s attorney.

If found guilty of destruction of property, the defendants could be fined up to $1,000 and face a maximum of 180 days behind bars.

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The New York Times first reported that three additional people had been charged with damaging the Reflecting Pool.

President Donald Trump has repeatedly claimed that vandals caused major damage to the pool by gashing the lining after his administration spent more than $14 million on renovations, though he has not provided evidence to support that claim. The officers who charged Carreno, Thiers and Dennison-Gibby did not accuse them of gashing the lining.

Former Olympic canoeist David Hearn was indicted by a grand jury in Washington, DC, last week for allegedly damaging the Reflecting Pool. Hearn — unlike Carreno, Thiers and Dennison-Gibby – was charged with destruction of property with a value of more than $1,000 which carries a maximum penalty of 10 years in prison, if convicted. He is set to be arraigned in court Thursday.

Crews began draining the Reflecting Pool over the weekend to make repairs, according to Interior Secretary Doug Burgum, for the second time in three months.

The move comes after weeks of problems – algae blooms, green-hued water, a chipping bottom and the administration’s allegations of vandalism – that have plagued the iconic landmark, making its woes the subject of national interest.

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Supreme Court financial disclosures reveal how their books add to their income

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Supreme Court financial disclosures reveal how their books add to their income

Supreme Court Justice Amy Coney Barrett speaks at the Reagan Library on Sept. 9, 2025, in Simi Valley, Calif. Barrett discussed and signed copies of her new book, Listening to the Law: Reflections on the Court and Constitution.

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Even as the Supreme Court was handing down one legal thunderbolt after another last week, the justices were quietly releasing their annual financial reports. Justice Samuel Alito was the only sitting justice to request an extension, which he has done for 15 years. The disclosures do not give a complete account of the justices’ total income and wealth, but they give insights into their concertgoing, guest professorships and even their involvement in youth sports.

In addition to their salaries, much of the justices’ reported income came from their book deals. Justice Ketanji Brown Jackson led the pack earning more than $1.1 million last year for a total of roughly $4 million since her memoir, Lovely One, was published in 2024.

Justices Sonia Sotomayor, Neil Gorsuch, Amy Coney Barrett and retired Justice Anthony Kennedy also reported income from published books. Earnings from their books ranged from $849,000 for Barrett, to $300,000 for Gorsuch and $88,000 for Sotomayor, whose books include her 2013 autobiography and five children’s books. Justice Clarence Thomas, who previously earned $1.5 million for his 2007 memoir, listed no publisher payments last year, and Justice Brett Kavanaugh, one of 13 co-authors of a 2016 legal treatise, also received no payments last year. Kavanaugh is said to be working on a memoir but he listed no payments for the anticipated book. Alito does have a book coming out in the fall, but with his financial report still outstanding, there is no data on how much he was paid for the work in 2025.

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The only two sitting justices who have not written books are Chief Justice John Roberts and Justice Elena Kagan.

Many justices also earned income from teaching at law schools. Roberts reported income from New England Law, located in Boston, and Gorsuch reported teaching income from George Mason University in Virginia. Thomas taught classes at Catholic University in Washington, D.C., and Barrett and Kavanaugh taught at Notre Dame Law School. Barrett graduated from the school and began teaching there 23 years ago; Kavanaugh has family connections to Notre Dame.

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Manhattan Building’s Columns Buckled Beneath New Addition, Images Show

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Manhattan Building’s Columns Buckled Beneath New Addition, Images Show

At least two structural columns buckled and failed in a 37-story office tower in Midtown Manhattan on Tuesday, prompting evacuations of nearby streets and buildings. While city officials asserted that the tower was in no danger of collapsing completely, outside engineers said further failures in the structure could not be ruled out.

A pair of columns that failed completely were part of the tower’s existing structure. A New York Times review of images and videos from inside the building has found that several floors were added atop these columns.

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City officials said in a news conference on Tuesday that the building was continuing to move, while they simultaneously assured the city that the building would not suffer “total collapse.” “The way this building is constructed, it’s a steel-frame building,” John Esposito, a chief in the Fire Department in New York, said at the afternoon news conference. “So, it would not be a total collapse. It would be more of a localized collapse.” Still, he said, “that remains our concern, that it’s moved.”

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Engineers said that the movement itself was cause for concern. In a properly designed steel building, they said, loads should redistribute quickly to surviving structural supports if columns failed.

Joe DiPompeo, a former president of the Structural Engineering Institute at the American Society of Civil Engineers, said that if the structure had been overloaded, he would expect any movement “to happen very quickly,” rather than gradually.

“Generally when a column buckles, it’s a sudden failure,” Mr. DiPompeo said. He said that a full collapse remained unlikely given the redundancies built into the building codes.

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Engineers often refer to the most dangerous possibility as a progressive collapse, a process in which structures near the initial failure become overstressed and also fail, potentially bringing down the building if the sequence continues. While unlikely, it cannot be ruled out, Mr. DiPompeo said.

Footage recorded from inside the building shows at least two structural columns appear to have failed completely, Mr. DiPompeo said. Other nonstructural, interior walls — or at least the metal “studs” that were in place to hold them up — also appear to have deformed.

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“The only way that really happens is if the floor above them dropped. It looks like the floor above could have dropped a foot or two, which is obviously not a good situation,” Mr. DiPompeo said.

@fernando40tiktok.commarc via Storyful

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Image from @fernando40tiktok.commarc via Storyful

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Image from @Bogs4NY via X

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The 37-story building is in the process of being converted from office space into residential units. Four new floors and a large vertical portion were added onto the existing building in recent months. The vertical portion consists of a stack of over a dozen new floors cantilevered out over the existing building below.

Engineers said that there was nothing inherently wrong with adding residential floors or the cantilevered section above the columns that failed, as long as the original structure and the modifications had properly accounted for the added weight and wind loads.

“The cantilever alone doesn’t change anything,” Mr. DiPompeo said, but it does put additional load on the columns underneath — a factor that should have been reflected in the design.

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Nathan Berman, managing principal and founder of MetroLoft, the developer overseeing the conversion, said on Tuesday that “this incident is nothing more than a typical construction mishap.”

He said two columns near the northwest corner of the tower had bent under the weight of additions to the building above, most likely because those columns had not been properly reinforced, though he said an investigation would determine the cause. The rest of the columns, he said, “picked up the weight.” He estimated the affected floors above the failed columns had sagged by a maximum of four inches.

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Mr. Berman said that he expected the problems to be fixed and the project to be completed with, at most, a slight delay.

On Tuesday evening, installation of temporary shoring was set to begin shortly, in order to help stabilize the 20th and 21st floors of the building.

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